Middletown, NY Homes for Sale

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  $399,900

  • 3 Beds
  • 2.5 Baths
  • 1,593 Sq Ft

  568 County Route 49 Unit 2C, Middletown, NY 10940

  FOR INVESTORS ONLY.... New townhouse on right side (Unit 2C) available in the Minisink Valley School District. This home welcomes you to an open foyer that leads to an updated kitchen with Quartz/Quartzite countertops and ample white cabinets. Lots of sunshine enters this home. The dining and living room area is spacious with beautiful floors. Huge closet that can be used as a pantry. A deck to

  

  Hazel Cello

  Keller Williams Hudson Valley

  (845) 328-4272

  568 County Route 49 Unit 2C, Middletown, NY 10940
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  /2

  $399,900

  • 5 Beds
  • 2 Baths
  • 2,440 Sq Ft

  44 Houston Ave, Middletown, NY 10940

  Excellent opportunity to own a 2 family house whether you are an investor or want to live in one of the units and rent the second one. Spacious apartments. First floor apartment has 3 bedrooms and 1 bathroom, second floor apartment has 2 bedrooms and 1 bath. Conveniently located, walking distance to Touro College where students are always looking for close by rentals. Minutes to I86 and I84,

  

  Dulce M Ferrera

  Keller Williams Hudson Valley

  (845) 497-6793

  44 Houston Ave, Middletown, NY 10940
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  /2

  $250,000

  • 3 Beds
  • 1 Bath
  • 1,120 Sq Ft

  13 Smith St, Middletown, NY 10940

  Looking to add a rental property to your porfolio? This 3 bedroom, 1 bathroom home might be the one. Long term tenant looking to stay. Located in the heart of the city of Middletown. Walking distance to local shops, restaurants, supermarket, park and much more. Located on a one way street with low local traffic. Call today for appoiintment.

  

  Dulce M Ferrera

  Keller Williams Hudson Valley

  (845) 299-0839

  13 Smith St, Middletown, NY 10940
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  $275,000 Open Sun 11AM - 1PM

  • 3 Beds
  • 1 Bath
  • 1,232 Sq Ft

  20 Columbia Ave, Middletown, NY 10940

  Step across the sun-warmed front walk, swing open the original door, and feel possibility bloom.Beneath time-worn rugs, early-century hardwood floors wait for their first gleam of daylight. Sunshine pours through tall windows, skimming vintage trim and setting off the solid brass door hardware that clicks shut with reassuring certainty. A welcoming living room flows into a private dining

  

  Brian Caplicki

  Keller Williams Hudson Valley

  (845) 671-5373

  20 Columbia Ave, Middletown, NY 10940
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  /50

  $899,000

  • 4 Beds
  • 2.5 Baths
  • 3,437 Sq Ft

  3 Kings Dr, Middletown, NY 10941

  Luxury Living in Hamptonburgh. Nestled in the prestigious Windsor Estates enclave, within the sought-after Goshen School District, this exceptional Contemporary residence offers a rare blend of elegance, comfort, and convenience. With nearly 3,500 sqft of thoughtfully designed living space, this striking home features 4 spacious bedrooms, 3 bathrooms, and a 3-car garage. Step into a grand

  

  Christina Rowan

  Howard Hanna Rand Realty

  (845) 393-3879

  3 Kings Dr, Middletown, NY 10941
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  /26

  $410,000

  • 4 Beds
  • 2 Baths
  • 1,668 Sq Ft

  31 Beattie Ave, Middletown, NY 10940

  Great 2 family home in the city of Middletown. Each apartment features 2 bedrooms, 1 bathroom. This property is located in a zoning that requires one of the apartments is occupied by the owner. House is well maintained and cared for. Large lot offers plenty of yard and parking. Walk-up attic offers plenty of storage. Each tenant has their own washer and dryer hook-up. Detached 2 car garage ideal

  

  Dulce M Ferrera

  Keller Williams Hudson Valley

  (845) 286-4605

  31 Beattie Ave, Middletown, NY 10940
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  /36

  $625,000

  • 4 Beds
  • 3.5 Baths
  • 2,760 Sq Ft

  214 Phillips St, Middletown, NY 10940

  Welcome to this beautiful newly built 4-bedroom, 3.5-bath home featuring a spacious 2,760 sqft layout across three levels of living space. The gourmet kitchen features an island with a breakfast bar and flows seamlessly into a large dining area. The luxurious primary suite includes a full ensuite bath with dual vanities, a shower, and a separate soaking tub, all highlighted by expansive windows.

  Donna Gray Redfin Real Estate

  214 Phillips St, Middletown, NY 10940
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  /23

  $490,000

  • 3 Beds
  • 2 Baths
  • 1,574 Sq Ft

  153 Ridgewood Ave Unit 155, Middletown, NY 10940

  WOW! Is what you will say as soon as you step into this almost like a new home, with an impressive open layout and all the amenities you are looking for. This thoughtfully designed, like new built ranch offers over 1,500 sq ft of stylish, low-maintenance living—all with modern upgrades, so you can relax without worrying about repairs or updates for years to come. Conveniently located near

  Emelisa Mendoza RE/MAX Town & Country

  153 Ridgewood Ave Unit 155, Middletown, NY 10940
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  $595,000

  • 5 Beds
  • 4 Baths
  • 3,890 Sq Ft

  1 Wawayanda Place, Middletown, NY 10940

  Discover this charming, recently renovated 5-bed, 3-bath home in Orange County, NY, boasting over 3,000 sq. ft. It offers resort-like amenities, perfect for short-term rentals. Explore nearby attractions like West Point, Storm King Art Center, Legoland New York, and Woodbury Common Premium Outlets. Showings by appointment only, Tuesdays to Thursdays, with pre-approval/proof of funds.

  Jamie Sittner Oxford Property Group USA

  1 Wawayanda Place, Middletown, NY 10940
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  /47

  $489,900

  • 2 Beds
  • 2 Baths
  • 1,473 Sq Ft

  84 Jasmine Dr, Middletown, NY 10940

  Welcome to 84 Jasmine Dr. in the highly desirable Wildflowers at Wallkill, a premier 55+ gated community offering resort-style living. This stunning 2011-built home features 2 bedrooms, 2 bathrooms, and an abundance of luxurious upgrades throughout. Step inside to a bright and spacious open floor plan with gorgeous Brazilian hardwood floors and elegant crown molding and wainscoting. The custom

  JoAnn Maxwell Howard Hanna Rand Realty

  84 Jasmine Dr, Middletown, NY 10940
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  $549,000

  • 3 Beds
  • 2.5 Baths
  • 2,929 Sq Ft

  1 Parkview Dr, Middletown, NY 10940

  Welcome to 1 Parkview Dr. in beautiful Presidential Park in Middletown, NY. Located on a corner lot, this expanded raised ranch shines. Gleaming hardwood floors and spacious room size are only some if it's great features. Eat in kitchen boasts an atrium that looks out to its lovely landscaped backyard. Spend time in this space and you'll feel like you're on vacation. Beautiful inground pool

  Marie Altieri Howard Hanna Rand Realty

  1 Parkview Dr, Middletown, NY 10940
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  $265,000

  • 2 Beds
  • 2 Baths
  • 1,146 Sq Ft

  162 Deer Ct Dr, Middletown, NY 10940

  Beautiful Condo in a Prime Location!Experience the perfect blend of comfort and convenience in this ideally located condo, perfect for commuters and those who love being close to the action. Just minutes from major highways, this home offers easy access to shopping centers, restaurants, and daily essentials.For city bound travelers, transportation is a breeze with nearby access to the Short Line

  Beverly Huaman Howard Hanna Rand Realty

  162 Deer Ct Dr, Middletown, NY 10940
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  $729,000

  • 4 Beds
  • 2.5 Baths
  • 3,856 Sq Ft

  446 M and M Rd, Middletown, NY 10940

  Luxury meets comfort in this spacious meticulously kept home with bonus room nestled on 3 lush, tree-lined acres in the desirable Pine Bush School District! Designed with both comfort and sophistication in mind, this residence features a 3-car garage with organized work area, central air, and an energy-efficient solar system. The gourmet kitchen includes granite counters, stainless steel

  Kismet Johnson eXp Realty

  446 M and M Rd, Middletown, NY 10940
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  /20

  $269,900

  • 2 Beds
  • 2.5 Baths
  • 880 Sq Ft

  147 Ruth Ct, Middletown, NY 10940

  Welcome to this beautifully maintained 2-bedroom, 2-bathroom condo in Middletown! Featuring a spacious and inviting layout, this condo boasts a generously sized primary bedroom with a walk-in closet. Conveniently located close to shops, restaurants, and entertainment, you'll love the ease of access to everything you need. Whether you're relaxing at home or exploring the vibrant local area, this

  Matthew Gibbs Keller Williams Hudson Valley

  147 Ruth Ct, Middletown, NY 10940
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  $465,000

  • 4 Beds
  • 3 Baths
  • 2,100 Sq Ft

  450 Mt Orange Rd, Middletown, NY 10940

  Welcome to this move in ready, spacious and versatile 4-bedroom, 3-bathroom bi-level home located in Minisink Valley School District. Thoughtfully designed and meticulously maintained, this home offers comfort, flexibility, and the potential for multigenerational living.Upstairs features 3 bedrooms and 2 full bathrooms, including a private en-suite in the primary bedroom. Gleaming

  Katrina Roloson Keller Williams Realty

  450 Mt Orange Rd, Middletown, NY 10940
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  $510,000

  • 4 Beds
  • 3 Baths
  • 2,160 Sq Ft

  612 Shoddy Hollow Rd, Middletown, NY 10940

  Located on one of the most scenic and peaceful roads in Orange County, this spacious mother-daughter home offers exceptional privacy on a full acre of land, just minutes from Middletown shopping, dining, and NYC train access. Tucked away on a quiet road, the home provides a rare sense of seclusion while still being close to everyday conveniences. Inside, you’ll find two full kitchens with

  Kewin Garabito eXp Realty

  612 Shoddy Hollow Rd, Middletown, NY 10940
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  /22

  $235,000

  • 2 Beds
  • 1 Bath
  • 974 Sq Ft

  38 Brittany Dr, Middletown, NY 10940

  Welcome to 38 Brittany Drive, located in a desirable ground-level condo nestled in a quiet, well-maintained community! This two-bedroom, one-bath unit features a functional galley kitchen with generous cabinetry, a spacious living area, and an in-unit washer/dryer for added convenience. Additionally, a 6x8 storage unit is located in the lower level (common area) of the basement. The monthly HOA

  Nicholas Cuomo Keller Williams Realty

  38 Brittany Dr, Middletown, NY 10940
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  /41

  $499,000

  • 7 Beds
  • 4 Baths
  • 2,652 Sq Ft

  8 Chestnut St, Middletown, NY 10940

  Stunning Fully Renovated 7-Bedroom Home in Downtown MiddletownStep into luxury with this beautifully renovated single-family home, perfectly situated on a quiet street in the heart of Downtown Middletown. Offering 7 spacious bedrooms and 4 modern baths, this home is designed for comfort and style.Key Features:Complete Renovation: Brand-new electrical, heating, plumbing, insulation, and windows

  Gitty Steinmetz Rodeo Realty Inc

  8 Chestnut St, Middletown, NY 10940
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  /23

  $479,000

  • 3 Beds
  • 2 Baths
  • 1,338 Sq Ft

  11 Dogwood Dr, Middletown, NY 10940

  Well maintained 3 bedroom, 2 bath Bilevel in an established residential neighborhood. This attractive home features Stainless Steel appliances, a Master Bedroom suite and a 1 car garage. Sq. Footage does not include an additional 774 sq. Ft. unfinished lower level, which could be a Family Room, Bedroom, .5 bath, or use your imagination. All window treatments will stay. Conveniently located

  Gloria Allan John J Lease REALTORS Inc

  11 Dogwood Dr, Middletown, NY 10940
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  $475,000

  • 4 Beds
  • 2 Baths
  • 2,036 Sq Ft

  51 Pine Ct, Middletown, NY 10941

  Beautiful Split Level home situated in one of the nicest areas of The Town Of Wallkill. This wonderful home offers an Open Airy Floor Plan, Gorgeous Harwood Floors on the First Floor, Brand New Designer Custom Kitchen with Quartz Countertops, Breakfast Bar, Stainless Steel Appliances, and Recessed Lighting. Large Sun Drenched Living Room with a Bay Window , spacious Dining Rm, Primary Bedroom

  John Biasi Howard Hanna Rand Realty

  51 Pine Ct, Middletown, NY 10941
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  $469,999

  • 3 Beds
  • 2 Baths
  • 1,268 Sq Ft

  338 Route 211 W, Middletown, NY 10940

  Welcome to your dream home! This meticulously renovated ranch-style residence in the heart of Middletown, NY, combines timeless charm with modern elegance. Carefully reimagined from top to bottom, this home features a bright, open-concept layout designed for both comfort and entertaining. At the heart of the home is a stunning, fully updated kitchen, showcasing rich dark cabinetry, sleek quartz

  Jeffrie Peña Locqube New York, Inc.

  338 Route 211 W, Middletown, NY 10940
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  /34

  $499,000

  • 4 Beds
  • 1.5 Baths
  • 2,722 Sq Ft

  391 Scotchtown Collabar Rd, Middletown, NY 10941

  Discover the Charm and Character of this circa 1800 four bedroom farmhouse colonial on 2.6 acres with a bedroom and bathroom on the main floor!! Do you dream of simpler times? Growing your own fruit herbs vegetables, and eggs? Starry nights in the back yard? It's all here and with many updates including a new roof. There is over 2700 square feet of living space, high ceilings (unheard of in

  John Biasi Howard Hanna Rand Realty

  391 Scotchtown Collabar Rd, Middletown, NY 10941
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  $480,000

  • 4 Beds
  • 2.5 Baths
  • 2,848 Sq Ft

  4 Thistle Ln, Middletown, NY 10940

  Spacious & Versatile Raised Ranch in Prime Middletown Location!Not your average bi-level! This move-in-ready, raised-ranch-style home in Middletown, within the Minisink Valley School District, offers the perfect blend of convenience and comfort. Located near Garnet Medical Center, Crystal Run, shopping centers, supermarkets, and with easy access to Metro-North and major highways, it’s an ideal

  Soleil Jackman Howard Hanna Rand Realty

  4 Thistle Ln, Middletown, NY 10940
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  $234,900

  • 2 Beds
  • 2 Baths
  • 880 Sq Ft

  143 Ruth Ct, Middletown, NY 10940

  A great Investment opportunity - - Low Taxes & Low Condo Fees. Currently leased. Tenant on a month to month lease @ $1,760 a month. Very quiet and well maintained condo complex. This first floor 2 bedroom, 2 bathroom condo offers a first floor King Sized master suite with walk in closet & full bathroom, a spacious living area with plenty of bright, natural light & a patio. The kitchen has

  Allan Leeds ON SITE Sales & Marketing, LLC

  143 Ruth Ct, Middletown, NY 10940
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  /2

  $525,000

  • 5 Beds
  • 4 Baths
  • 3,140 Sq Ft

  7 Highland View Place, Middletown, NY 10940

  Welcome home to this beautifully maintained 5-bedroom, 4-bathroom raised ranch, ideally situated near the highly-rated Presidential Park Elementary School in Middletown, NY. Perfect for growing families or multi-generational living, this expansive home offers generous living space, natural light throughout, and thoughtful updates that make it move-in ready.Step inside to discover an open-concept

  Hilary Hemans-Mensah Keller Williams Realty

  7 Highland View Place, Middletown, NY 10940
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  $369,000

  • 3 Beds
  • 1.5 Baths
  • 1,564 Sq Ft

  38 Wilson St, Middletown, NY 10940

  Welcome to 38 Wilson where charm, space, and potential come together.This 3-bedroom, 1.5-bath split-level home offers a fresh start with newly painted interiors and a layout full of possibility. Step inside to soaring cathedral ceilings and a bright open-concept kitchen, perfect for both everyday living and entertaining. Upstairs features three generously sized bedrooms and a full bathroom.

  Pete Koutros Keller Williams Hudson Valley

  38 Wilson St, Middletown, NY 10940
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  $399,900 Open Sun 12PM - 2PM

  • 3 Beds
  • 1 Bath
  • 1,908 Sq Ft

  151 School House Rd, Middletown, NY 10940

  Peaceful 5-Acre Retreat in Minisink Valley School District – 151 Schoolhouse Rd, Middletown, NY -Welcome to 151 Schoolhouse Rd – a private 5-acre sanctuary nestled on a quiet country road in the sought-after Minisink Valley School District. This spacious bilevel home offers over 1,900 sq ft of comfortable living space, combining modern updates with serene, natural surroundings.Upstairs,

  Alyse Toffel Keller Williams Hudson Valley

  151 School House Rd, Middletown, NY 10940
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  /2

  $210,000 Open Sat 10AM - 12PM

  • 2 Beds
  • 2 Baths
  • 880 Sq Ft

  181 Ruth Ct, Middletown, NY 10940

  More pictures and details coming soon for this end-unit two-bed, two-full-bath ground-level condo in Eastview Condominium!

  Nicholas Cuomo Keller Williams Realty

  181 Ruth Ct, Middletown, NY 10940
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  $169,000

  • 1 Bed
  • 1 Bath
  • 735 Sq Ft

  324 Concord Ln, Middletown, NY 10940

  Welcome to this beautiful condo in the Buttonwood Hills complex! This bright and spacious unit features a combined living and dining area with sliding doors that lead to a private deck—perfect for relaxing or enjoying your morning coffee. The kitchen is equipped with stainless steel appliances. There is one generously sized bedroom and one full bathroom, tastefully upgraded with modern finishes,

  Wenpeng Guan Keller Williams Hudson Valley

  324 Concord Ln, Middletown, NY 10940
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  /17

  $175,000 Open Sat 11AM - 1PM

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft

  42 Inwood Rd, Middletown, NY 10941

  This well-maintained ground-floor condo offers a blend of comfort & style with updates completed in 2017. Featuring modern flooring, updated doors & a renovated bathroom. The kitchen boasts granite counters, a tiled backsplash and stainless steel appliances-all installed during the renovation. The spacious bedroom includes a large walk-in closet, and the open living/dining area offers flexible

  Gloria Rivera Keller Williams Hudson Valley

  42 Inwood Rd, Middletown, NY 10941
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  /35

  $650,000

  • 9 Beds
  • 3 Baths

  11 East Ave, Middletown, NY 10940

  Attention Investors & Savvy Buyers! Don’t miss this incredible opportunity to own a fully renovated three-family home in the heart of Middletown. Perfectly located within walking distance to public transportation, schools, parks, and shopping, this property offers convenience and strong rental potential. Each of the three spacious units features 3 bedrooms and 1 full bathroom, all newly renovated

  Susan Giordano John J Lease REALTORS Inc

  11 East Ave, Middletown, NY 10940
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  $429,999

  • 2,946 Sq Ft

  221 E Main St, Middletown, NY 10940

  Welcome to 221 E Main St—a standout investment opportunity offering flexibility, location, and long-term potential in one of Orange County’s most active and rapidly growing markets. This mixed-use property features two residential units and a commercial space on the ground floor, making it an ideal choice for investors, owner-occupants, or entrepreneurs looking to establish a business while

  Savannah Miceli Century 21 Alliance Rlty Group

  221 E Main St, Middletown, NY 10940
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  /40

  $205,000

  • 2,269 Sq Ft

  97 E Main St, Middletown, NY 10940

  Don’t miss your chance to own a versatile property in one of Orange County’s fastest-growing areas. Located in the heart of Middletown, this mixed-use building offers a unique opportunity for both residential living and commercial investment in a high-demand market. Just 70 miles from New York City, Middletown offers the perfect blend of suburban comfort and urban accessibility, with direct

  Savannah Miceli Century 21 Alliance Rlty Group

  97 E Main St, Middletown, NY 10940
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  /50

  $2,999,999 Open Sun 12PM - 2PM

  • 5 Beds
  • 4.5 Baths
  • 6,460 Sq Ft

  285 Hill Rd, Middletown, NY 10940

  Great potential to embrace an equestrian lifestyle with immediate income producing potential. This Training Center features 29 acres of sprawling green grounds and incredible views. As you pass through the gated entrance, you will experience a world of equestrian wonder. The main barn boasts 13 stalls and an attached 75'x133' indoor arena with sprinkler system, over $500,000 cost. Two large

  Warren Shelley Reliable Realty Group

  285 Hill Rd, Middletown, NY 10940
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  /21

  $425,000

  • 3 Beds
  • 1.5 Baths
  • 1,620 Sq Ft

  76 Maureen Dr, Middletown, NY 10940

  Welcome to Robins Meadows, one of the area's most sought-after neighborhoods, where this charming raised ranch sits proudly on a spacious corner lot. Featuring 3 bedrooms and 1.5 baths, this home offers the perfect blend of comfort, functionality, and location. The main level features an open living and dining area, while the lower level offers additional flexible space complete with a cozy

  Nina Piacente Julia B Fee Sothebys Int. Rlty

  76 Maureen Dr, Middletown, NY 10940
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  /42

  $340,000

  • 3 Beds
  • 1.5 Baths
  • 1,540 Sq Ft

  45 Birch Dr, Middletown, NY 10940

  Welcome to 45 Birch Drive, a beautifully renovated and move-in-ready 3-bedroom, 1.5-bath townhouse offering modern updates, spacious living, and everyday comfort.Step inside to a bright and inviting layout updated lighting, and a flowing main level perfect for both relaxing and entertaining. The kitchen has been refreshed with modern appliances and custom cabinetry, offering style and

  Christopher Baum RE/MAX Benchmark Realty Group

  45 Birch Dr, Middletown, NY 10940
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  /45

  $449,000

  • 4 Beds
  • 2.5 Baths
  • 2,000 Sq Ft

  7 Ross Ln, Middletown, NY 10941

  THIS IS THE ONE!! Wonderful family home in the heart of Scotchtown. FIRST time on the market in over half a century!! Well maintained, must see to believe! Located on over 1/3 of an acre, this home is one of a kind! Hardwood floors throughout the home have been recently treated. The eat in kitchen provides convenience AND easy access to the HUGE, two-tiered back deck. The home offers a Formal

  David Furlin BHHS Hudson Valley Properties

  7 Ross Ln, Middletown, NY 10941
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  /23

  $330,000

  • 2 Beds
  • 2.5 Baths
  • 1,831 Sq Ft

  12 Deer Ct Dr, Middletown, NY 10940

  Spacious Townhouse in a Prime Location!This well-located townhouse offers the perfect combination of space, comfort, and convenience. Ideal for commuters and anyone who enjoys being close to all the action. Just minutes from major highways, the home provides easy access to shopping centers, restaurants, and everyday essentials. For city bound travelers, getting around is simple. With nearby

  Beverly Huaman Howard Hanna Rand Realty

  12 Deer Ct Dr, Middletown, NY 10940
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  /28

  $415,000

  • 4 Beds
  • 2 Baths
  • 1,848 Sq Ft

  21 Maple Dr, Middletown, NY 10940

  Move right into this charming cape cod style home. 4 oversized bedroom’s and 2 full bathrooms. Step out onto a second story oversized deck from one of the two massive upstair bedrooms. The home is packed with updates, including new flooring throughout, a cozy kitchen and a large bay window in the living room that maximizes natural lighting. A detached garage with plenty of storage in the loft

  David Ferstand Daf Realty

  21 Maple Dr, Middletown, NY 10940
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  /38

  $585,000

  • 3 Beds
  • 2 Baths
  • 4,240 Sq Ft

  83 Dosen Rd, Middletown, NY 10940

  Welcome to your private retreat, perfectly nestled on 4.6 scenic, park-like acres in the heart of the Pine Bush School District. This 1 owner home has 3 bedrooms 2 baths on 1st level, screened in porch off kitchen, enormous living room offers plenty of room for the whole family plus extended family and is ideal for those who love to entertain or simply enjoy the peaceful Hudson Valley lifestyle.

  Joseph Rubeo Keller Williams Hudson Valley

  83 Dosen Rd, Middletown, NY 10940

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